EP1909599A1 - Utilisation d'hesperetine pour developper le gout sucre - Google Patents

Utilisation d'hesperetine pour developper le gout sucre

Info

Publication number
EP1909599A1
EP1909599A1 EP06777960A EP06777960A EP1909599A1 EP 1909599 A1 EP1909599 A1 EP 1909599A1 EP 06777960 A EP06777960 A EP 06777960A EP 06777960 A EP06777960 A EP 06777960A EP 1909599 A1 EP1909599 A1 EP 1909599A1
Authority
EP
European Patent Office
Prior art keywords
sweet
hesperetin
formula
salts
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP06777960A
Other languages
German (de)
English (en)
Other versions
EP1909599B1 (fr
Inventor
Jakob Ley
Günter Kindel
Susanne Paetz
Thomas Riess
Martin Haug
Ralph Schmidtmann
Gerhard Krammer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Priority to EP10190555.2A priority Critical patent/EP2368442B1/fr
Priority to PL06777960T priority patent/PL1909599T3/pl
Publication of EP1909599A1 publication Critical patent/EP1909599A1/fr
Application granted granted Critical
Publication of EP1909599B1 publication Critical patent/EP1909599B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • sweet-tasting substance or sweet-tasting substances include one or more sugar(s), wherein the quantity of (i) hesperitin or (ii) the salts thereof is sufficient to impart the same or an enhanced sweet impression, compared with a preparation which, with an otherwise identical composition, contains neither (i) hesperetin nor the salts thereof but at least 1.05 times, preferably at least 1.4 times, the amount of sugar.
  • the sugars are preferably selected in this case from the group comprising: sucrose, lactose, glucose, fructose and mixtures thereof.
  • soya milk and products produced therefrom soya lecithin-containing preparations, fermented products such as tofu or tempe or products produced therefrom, soya sauces), fruit preparations (e.g. preserves, sorbets, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, vegetables pickled in vinegar, preserved vegetables), snacks (e.g. backed or fried potato crisps or potato dough products, bread dough products, extrudates based on maize or peanut), products based on fat or oil or emulsions thereof (e.g.
  • the preparations according to the invention used for oral hygiene are in particular oral and/or dental care products, such as toothpastes, tooth gels, tooth powder, mouthwashes, chewing gums and other oral hygiene products.
  • the preparations according to the invention containing hesperetin and/or the salts thereof are produced according to a preferred embodiment by incorporating the hesperetin of formula (I) and/or the salts thereof as a substance, as a solution (e.g. in ethanol, water, 1,2-propylene glycol, dimethylsulphoxide) or in the form of a mixture with a solid or liquid carrier (e.g. maltodextrin, starch, silica gel), flavours or flavourings and optionally further auxiliaries and/or stabilisers (e.g. natural or synthetic polysaccharides and/or plant gums, such as modified starches or gum arabic) in a base preparation used for nourishment, oral hygiene or consumption.
  • a solution and/or suspension or emulsion may advantageously also be converted by spray drying into a solid preparation according to the invention (semi-finished product).
  • the spray-dried, solid preparations according to the invention are particularly suitable as semi-finished products for producing further preparations according to the invention as the solubility of the hesperetin and/or the salts thereof to be used according to the invention is significantly improved by the carriers and/or auxiliaries, in particular by maltodextrin, starch, natural or synthetic polysaccharides and/or plant gums, such as modified starches or gum arabic.
  • hesperetin and/or the salts thereof to be used according to the invention and optionally other constituents of the preparation according to the invention are incorporated firstly into emulsions, liposomes, e.g. starting from phosphatidylcholine, microspheres, nanospheres or in capsules, granules or extrudates of a matrix suitable for foods and semi -luxury foods, e.g. of starch, starch derivates (e.g. modified starch), cellulose or cellulose derivates (e.g. hydroxypropyl cellulose), other polysaccharides (e.g.
  • dextrin alginate, curdlan, carrageenan, chitin, chitosan, pullulan
  • natural fats natural waxes (e.g. beeswax, camauba wax)
  • proteins e.g. gelatines or other natural products (e.g. shellac)
  • the products may also be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally a suitable combination of said processes.
  • a chewing compound that plasticises on chewing, various types of sugar, sugar substitutes, other sweet- tasting substances, sugar alcohols, taste corrigents for unpleasant taste impressions, other taste modulators for further, generally not unpleasant taste impressions, taste-modulating substances (e.g. inositolphosphate, nucleotides such as guanosinmonophosphate, adenosinmonophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavours and stabilisers or odour corrigents.
  • taste-modulating substances e.g. inositolphosphate, nucleotides such as guanosinmonophosphate, adenosinmonophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • humectants e.g. inositolphosphate, nucleotides such as guanosin
  • the hesperetin and/or the salts thereof to be used according to the invention are used in the preparations according to the invention in combination with at least one (further) substance capable of masking or reducing an unpleasant (bitter, chalky, acidic, astringent) taste impression or for enhancing a pleasant taste impression (sweet, salty, savoury).
  • a particularly effective enhancement of the sweetness may thus be achieved, for example.
  • the combination of the hesperetin or salts thereof to be used according to the invention with taste corrigents for unpleasant, in particular bitter, taste impressions or flavour enhancers for pleasant, in particular sweet, taste impressions is preferred in particular.
  • hesperetin of formula (I) is in the form of a (2S)-enantiomer, (2f?)- enantiomer or any desired mixture of the two enantiomers,
  • sweet-tasting substance(s) one or more further (iii) sweet-tasting substance(s) and/or (iv) flavouring(s) which give(s) a sweet olfactory impression,
  • Preparation according to any one of embodiments 7 or 8, comprising in total 0.0001 % by weight to 95 % by weight, preferably 0.001 % by weight to 80 % by weight, particularly preferably 0.001 % by weight to 50 % by weight, based on the total weight of the preparation of (i) hesperetin and (ii) the salts thereof.
  • the primary object of the present invention was to find substances which (a) are selectively suitable for enhancing the sweet taste of a sweet-tasting substance and/or the sweet olfactory impression of a flavouring which gives a sweet olfactory impression, preferably without adversely affecting the remaining flavour profile, (b) can be widely used and (c) preferably occur naturally, preferably in foods or semi-luxury foods or the corresponding raw materials for the preparation thereof or are formed during the production of foods or semi-luxury foods.
  • salts of the hesperetin of the above formula (I) to be used according to the invention one, a plurality of or all group(s) of the hesperetin that can be deprotonated are deprotonated.
  • counterions wherein these are preferably selected from the group comprising: singly positively charged cations of the first primary and secondary group, ammonium ions, trial kylammonium ions, doubly positively charged cations of the second primary and secondary group and trebly positively charged cations of the third primary and secondary group and mixtures thereof.
  • one or more carbohydrates selected from the group comprising sucrose, trehalose, lactose, maltose, melizitose, melibiose, raff i nose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D- mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceraldehyde, maltodextrin and vegetable preparations containing one or more of said carbohydrate(s), (preferably in a content of at least 5 % by weight, preferably at least 15 % by weight), wherein these carbohydrates may also be in the form of a natural or synthetically produced mixture (e.g. as a honey, invert sugar syrup, highly enriched fructose syrups made from corn starch [high fructose corn syrup])
  • these carbohydrates may also be in the form of
  • acetic acid-n-butylester acetic acid isoamylester, propionic acid ethylester, ethyl butyrate, butyric acid-n- butylester, butyric acid isoamylester, 3-methylethyl butyrate, n-caproic acid ethylester, n-caproic acid allylester, n-caproic acid-n-butylester, n-octanoic acid ethylester, ethyl-3-methyl-3-phenylglycidate, ethyl-2-trans-4-cis-decadienoate), 4- (p-hydroxyphenyl)-2-butanone, 1 ,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6- dimethyl-5-hepten-1-al and phenylacetaldehyde.
  • sweet-tasting substances selected from the group comprising:
  • sucrose, lactose, D-glucose, D-tagatose and D-fructose wherein these carbohydrates may also be in the form of natural or synthetically produced mixtures (e.g. as a honey, invert sugar syrup, highly enriched fructose syrups made from corn starch [high fructose corn syrup])
  • sweeteners from the group comprising sodium cyclamate, acesulfame K, neohesperidin dihydrochalcone, saccharin sodium salt, aspartame, superaspartame, neotame, alitame, sucralose, stevioside,
  • the quantity of added (i) hesperetin and (ii) the salts thereof in the preparation is sufficient to enhance in sensory terms the sweet taste impression of the sweet-tasting substance(s).
  • the total quantity of hesperetin of formula (I) and/or the salts thereof is preferably in the range of 0.1 to 500 ppm, particularly preferably in the range of 1 to 250 ppm, particularly preferably in the range of 5 to 100 ppm, based on the total weight of the preparation.
  • a synergistic increase in the sweet taste impression can be achieved in particular with these combinations (as mentioned above).
  • hemandulcin isocoumarins such as phyllodulcin or hydrangenol, dihydrochalcone glycosides, such as neohesperidin dihydrochalcone, glycyrrhizin, glycyrrhetinic acid ammonium salt or other glycyrrhetinic acid derivatives), liquorice extracts (Glycyrrhizza glabra ssp.), Lippia dulcis extracts, Momordica ssp. extracts or individual substances (in particular Momordica grosvenori [Luo Han Guo] and the mogrosides obtained therefrom), Hydrangea dulcis or Stevia ssp. (e.g. Stevia rebaudiana) extracts or individual substances.
  • dihydrochalcone glycosides such as neohesperidin dihydrochalcone, glycyrrhizin, glycyrrhetinic acid
  • flavourings which give a sweet olfactory impression, i.e. flavourings which do not taste sweet in the narrower sense but suggest a sweet taste in the wider sense (including odour perception in particular).
  • the sweet taste of a sweet-tasting substance or the sweet olfactory impression of a flavouring which gives a sweet olfactory impression is preferably enhanced in a preparation used for nourishment (foods), oral hygiene or consumption (semi- luxury foods).
  • the hesperetin and/or the salts thereof or corresponding mixtures used significantly enhance(s) the sensory effect of sweet-tasting substances or flavourings which give a sweet olfactory impression.
  • the preparations used according to the invention for nourishment, oral hygiene or consumption are generally products which are intended to be introduced into the human oral cavity, remain there for a certain time and are either subsequently consumed there (e.g. ready-to-consume foods) or are removed from the oral cavity again (e.g. chewing gum or toothpaste). It is understood that the use of the hesperetin of formula (I) and/or the salts thereof or corresponding mixtures to be used according to the invention is provided for all manner of products of this kind.
  • Preparations according to the invention which are in the form of semi-finished products can be used in particular for enhancing the sweet taste impression of finished product preparations used for nourishment, oral hygiene or consumption which are produced by using the semi-finished product preparation.
  • compositions according to the invention are carbohydrates and/or carbohydrate polymers (polysaccharides).
  • a preferred preparation according to the invention comprises as additional component (d)
  • Said esters can be in the form of all possible stereoisomers as pure substances or mixtures of the possible stereoisomers, depending on the underlying acid.
  • Perfume, flavouring or flavour compositions according to the invention which include the above-mentioned esters or solvents, induce very good solubility and prevent a significant tendency toward recrystallisation of the hesperetin of formula (I) and/or the salts thereof and corresponding mixtures to be used according to the invention. They are therefore particularly suitable for incorporation into preparations used according to the invention for nourishment, oral hygiene or consumption. Reference is made to the above statements with respect to the preferred concentrations of hesperetin or salts in perfume, flavouring or flavour compositions according to the invention.
  • dextrin alginate, curdlan, carrageenan, chitin, chitosan, pullulan
  • natural fats natural waxes (e.g. beeswax, carnauba wax)
  • proteins e.g. gelatines or other natural products (e.g. shellac) for producing the preparations according to the invention.
  • the products may be obtained, depending on the matrix, by spray drying, spray granulation, melt granulation, fluidised bed processes (e.g. according to WO 97/16078 or WO 2004/022642), fluidised bed spray granulation (e.g.
  • carotinoids flavonoids, anthocyans, chlorophyll and the derivatives thereof
  • spices trigeminally active substances or plant extracts containing such trigeminally active substances, synthetic, natural or nature- identical flavourings or perfumes and odour corrigents.
  • a particularly preferred combination thus results owing to the use of the hesperetin of formula (I) and/or the salts thereof or corresponding mixtures, together with 4-hydroxydihydrochalcones or salts thereof (in particular the Na + , K + , NH 4 + , Ca 2+ , Mg 2+ , Al 3+ and/or Zn 2+ salts) for enhancing the sweetness of the above-mentioned sweet-tasting substances, in particular of sugars.
  • 4-hydroxydihydrochalcones or salts thereof in particular the Na + , K + , NH 4 + , Ca 2+ , Mg 2+ , Al 3+ and/or Zn 2+ salts
  • Preparations according to the invention may also be in the form of capsules, tablets (uncoated and coated tablets, e.g. gastric juice-resistant coatings), sugar- coated pills, granules, pellets, solid mixtures, dispersions in liquid phases, emulsions, powders, solutions, pastes or other preparations that can be swallowed or chewed as a food supplement.
  • tablets uncoated and coated tablets, e.g. gastric juice-resistant coatings
  • sugar- coated pills e.g. gastric juice-resistant coatings
  • component (b) mixing one or more sweet-tasting substance(s) (component (b)) or one or more flavouring(s) which give(s) a sweet olfactory impression (component (c)) with a total quantity of a component (a) as it is defined above, i.e. with a total quantity of a hesperetin of formula (I) and/or (ii) a corresponding salt or corresponding mixture, wherein the total quantity of component (a) in the preparation is sufficient to enhance in sensory terms the sweet taste impression of the sweet-tasting substance(s) (b) or the sweet olfactory impression of the flavouring(s) (c) which give(s) a sweet olfactory impression.
  • the ingredients were mixed in the given order.
  • the resultant product can be used as a sweetener for foods or semi-luxury foods, e.g. coffee or tea.
  • An ice cream suitable for diabetics was produced from the following ingredients and decanted into tubs in portions of 95 ml_ each:
  • vanilla flavour containing vanilla pod extract, vanillin and 1 % by weight hesperetin, based on the total weight of the vanilla aroma.
  • a chocolate suitable for diabetics was produced from the following ingredients and poured into rectangular blocks:
  • Polydextrose is a polysaccharide which does not itself taste sweet and has a low calorific value.
  • the gelatine capsules suitable for direct consumption were produced according to WO 2004/050069 and had a diameter of 5 mm, the weight ratio of core material to casing material was 90:10.
  • the capsules opened in the mouth within less than 10 seconds and dissolved completely within less than 50 seconds.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Seasonings (AREA)
  • Confectionery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention concerne l'utilisation d'hespérétine de formule (I), ladite hespérétine de formule (1) étant sous la forme d’un énantiomère (2S), d’un énantiomère (2R), ou de tout mélange désiré des deux énantiomères, d'un sel d'hespérétine de formule (I), d'un mélange comprenant ou consistant en deux sels d'hespérétine de formule (I) ou plus, ou d'un mélange comprenant ou consistant en l'hespérétine de formule (I) et un ou plusieurs sels d'hespérétine de formule (I), pour développer le goût sucré d'une substance à goût sucré, ou la sensation olfactive sucrée d'un arôme donnant une sensation olfactive sucrée.
EP06777960.3A 2005-07-27 2006-07-25 Utilisation d'hesperetine pour developper le gout sucre Active EP1909599B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP10190555.2A EP2368442B1 (fr) 2005-07-27 2006-07-25 Utilisation d'hespérétine pour améliorer le goût sucré
PL06777960T PL1909599T3 (pl) 2005-07-27 2006-07-25 Zastosowanie hesperetyny do wzmacniania słodkiego smaku

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US70294305P 2005-07-27 2005-07-27
US78444406P 2006-03-22 2006-03-22
PCT/EP2006/064633 WO2007014879A1 (fr) 2005-07-27 2006-07-25 Utilisation d'hesperetine pour developper le gout sucre

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP10190555.2A Division-Into EP2368442B1 (fr) 2005-07-27 2006-07-25 Utilisation d'hespérétine pour améliorer le goût sucré
EP10190555.2A Division EP2368442B1 (fr) 2005-07-27 2006-07-25 Utilisation d'hespérétine pour améliorer le goût sucré

Publications (2)

Publication Number Publication Date
EP1909599A1 true EP1909599A1 (fr) 2008-04-16
EP1909599B1 EP1909599B1 (fr) 2014-04-23

Family

ID=37023144

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06777960.3A Active EP1909599B1 (fr) 2005-07-27 2006-07-25 Utilisation d'hesperetine pour developper le gout sucre

Country Status (10)

Country Link
US (1) US8679461B2 (fr)
EP (1) EP1909599B1 (fr)
JP (1) JP2009502153A (fr)
CN (1) CN101247734B (fr)
AR (1) AR054585A1 (fr)
BR (1) BRPI0613854B1 (fr)
CA (1) CA2613722A1 (fr)
ES (1) ES2466291T3 (fr)
PL (1) PL1909599T3 (fr)
WO (1) WO2007014879A1 (fr)

Cited By (8)

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EP2529632A1 (fr) 2011-05-31 2012-12-05 Symrise AG Acide aminé cinnamique comme arômes épicés
EP2742983A1 (fr) 2012-12-11 2014-06-18 Symrise AG Procédé permettant d'isoler des composés d'arôme et de parfum
WO2017121855A1 (fr) 2016-01-15 2017-07-20 Universität Hamburg Composés de type flavonoïde portant un résidu o-rhamnosyle
WO2017186298A1 (fr) 2016-04-28 2017-11-02 Symrise Ag Dérivés de dihydrochalcone influençant des états inflammatoires
WO2017220127A1 (fr) 2016-06-21 2017-12-28 Symrise Ag Utilisation de composés déterminés pour modifier, atténuer ou faire disparaître des notes indésirables
WO2018001703A1 (fr) * 2016-06-30 2018-01-04 Firmenich Sa Produits alimentaires et de boisson aromatisés
WO2018095533A1 (fr) 2016-11-25 2018-05-31 Symrise Ag Mélanges ayant des propriétés stabilisantes
EP3704954A1 (fr) 2019-03-05 2020-09-09 Symrise AG Mélange comprenant d-allulose et composés de modification du goût

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EP1909599B1 (fr) 2005-07-27 2014-04-23 Symrise AG Utilisation d'hesperetine pour developper le gout sucre
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
EP1955601A1 (fr) 2007-01-25 2008-08-13 Symrise GmbH & Co. KG Utilisation de propenylphenylglucosides afin de renforcer les impressions sensorielles de la douceur
EP2129240A4 (fr) * 2007-02-23 2010-03-17 Miles Loren Compositions édulcorantes entièrement naturelles
JP4912923B2 (ja) * 2007-02-28 2012-04-11 森永乳業株式会社 コーヒー配合飲食品用組成物
US8778987B2 (en) 2007-03-13 2014-07-15 Symrise Ag Use of 4-hydroxychalcone derivatives for masking an unpleasant taste
EP1977655B1 (fr) 2007-03-29 2011-05-18 Symrise AG Compositions d'aromes d'alcamides comprenant de l'hespérétine et/ou des 4-hydroxydihydrochalcones et leurs sels destinées à renforcer les impressions sensorielles sucrées
JP4892710B2 (ja) * 2007-04-27 2012-03-07 東洋精糖株式会社 高甘味度甘味料
DE502008000732D1 (de) 2007-05-08 2010-07-15 Symrise Gmbh & Co Kg Substituierte Cyclopropancarbonsäure(3-methyl-cyclohexyl)amide als Geschmacksstoffe
EP2008530B1 (fr) 2007-06-19 2011-01-19 Symrise AG Composition d'aromes destinée à réduire ou à supprimer une impression indésirable amère et astringente
ES2395682T3 (es) 2007-08-20 2013-02-14 Symrise Ag Derivados de ácido oxálico y su uso como principios activos refrescantes fisiológicos
EP2064959B1 (fr) 2007-10-31 2012-07-25 Symrise AG Néomenthylamides aromatiques en tant qu'agents aromatisants
EP2135516B1 (fr) 2008-06-13 2012-08-15 Symrise AG Néo-dérivés de menthyle en tant qu'arômes artificiels
US8043645B2 (en) 2008-07-09 2011-10-25 Starbucks Corporation Method of making beverages with enhanced flavors and aromas
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BRPI0613854B1 (pt) 2015-08-11
CA2613722A1 (fr) 2007-02-08
ES2466291T3 (es) 2014-06-09
JP2009502153A (ja) 2009-01-29
EP1909599B1 (fr) 2014-04-23
WO2007014879A8 (fr) 2007-05-18
PL1909599T3 (pl) 2014-10-31
BRPI0613854A2 (pt) 2011-02-15
WO2007014879A1 (fr) 2007-02-08
CN101247734A (zh) 2008-08-20
AR054585A1 (es) 2007-06-27
US20080305052A1 (en) 2008-12-11
US8679461B2 (en) 2014-03-25

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